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Acrylamide → (2S)-N2-[(3S)-1-(aminocarbonylethyl)pyrrolidin-3-yl]-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide

HRID 841924
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HRID 841924 반응식
[C:1]([NH2:5])(=[O:4])[CH:2]=[CH2:3].[O:6]1[C:10]2[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=2[N:8]=[C:7]1[N:15]1[CH2:20][CH2:19][CH2:18][CH2:17][C@H:16]1[C:21]([NH:23][C@H:24]1[CH2:28][CH2:27][NH:26][CH2:25]1)=[O:22]>C(OCC)C.O>[NH3:5].[NH2:5][C:1]([CH2:2][CH2:3][N:26]1[CH2:27][CH2:28][C@H:24]([NH:23][C:21]([C@@H:16]2[CH2:17][CH2:18][CH2:19][CH2:20][N:15]2[C:7]2[O:6][C:10]3[CH:11]=[CH:12][CH:13]=[CH:14][C:9]=3[N:8]=2)=[O:22])[CH2:25]1)=[O:4]
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참가 물질

6

반응물 2

HCID 6579AcrylamideHCID 57068119(2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)-pyrrolidin-3-yl]-2-piperidinecarboxamide

생성물 2

HCID 222AmmoniaHCID 57170845(2S)-N2-[(3S)-1-(aminocarbonylethyl)pyrrolidin-3-yl]-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide수율 83.9%

시약·촉매·용매 2

HCID 962Water용매
HCID 3283
Diethyl Ether
용매

실험 절차

Acrylamide (11.6 mg) was added to a solution of (2S)-1-(1,3-benzoxazol-2-yl)-N2-[(3S)-pyrrolidin-3-yl]-2-piperidinecarboxamide (51.6 mg) [see Example 4] in diethyl ether (3ml). The reaction mixture was refluxed for 18 hours, after which time the ethereal layer was diluted with water. The aqueous layer was separated and then extracted with ethyl acetate. The combined organic layers were dried over magnesium sulphate and the solvent removed under reduced pressure. The crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 93:7:1, changing to 90:10:1, dichloromethane:methanol: 0.88 aqueous ammonia solution to afford (2S)-N2-[(3S)-1-(aminocarbonylethyl)pyrrolidin-3-yl]-1-(1,3-benzoxazol-2-yl)-2-piperidinecarboxamide (26.4 mg) as an off-white foam.

후처리

  1. temperatureThe reaction mixture was refluxed for 18 hours
  2. customThe aqueous layer was separated
  3. extractionextracted with ethyl acetate
  4. dry with materialThe combined organic layers were dried over magnesium sulphate
  5. customthe solvent removed under reduced pressure
  6. customThe crude product was purified by column chromatography on silica gel eluting with a solvent gradient of 93:7:1

출처 및 근거

ORD 기록
ord-85ee1ca93b4648fb925419d8cb757c1e
출처 데이터셋
uspto-grants-2002_04
DOI
10.6084/m9.figshare.5104873.v1
특허 번호
US06372736B1

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